Knölker-Type Iron Complexes Bearing an N-Heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides

Knölker-Type Iron Complexes Bearing an N-Heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides

A family of iron Knolker-type complexes bearing an N-heterocyclic carbene (NHC) ligand has been synthesized from the corresponding tricarbonyl(η4-cyclopentadienone)iron complex by reaction with the in situ generated NHC ligand, under UV irradn. (350 nm) at room temp. The six complexes, obtained in g...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organometallics 2015-09, Vol.34 (18), p.4521-4528
Hauptverfasser: Elangovan, Saravanakumar, Quintero-Duque, Samuel, Dorcet, Vincent, Roisnel, Thierry, Norel, Lucie, Darcel, Christophe, Sortais, Jean-Baptiste
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4528
container_issue 18
container_start_page 4521
container_title Organometallics
container_volume 34
creator Elangovan, Saravanakumar
Quintero-Duque, Samuel
Dorcet, Vincent
Roisnel, Thierry
Norel, Lucie
Darcel, Christophe
Sortais, Jean-Baptiste
description A family of iron Knolker-type complexes bearing an N-heterocyclic carbene (NHC) ligand has been synthesized from the corresponding tricarbonyl(η4-cyclopentadienone)iron complex by reaction with the in situ generated NHC ligand, under UV irradn. (350 nm) at room temp. The six complexes, obtained in good yields (64-84%) after purifn. on column chromatog., were fully characterized, including X-ray diffraction and electrochem. studies. The activity of these complexes in catalysis has been demonstrated for the dehydration of primary benzamides into benzonitriles under hydrosilylation conditions using inexpensive polymethylhydrosiloxane (PMHS) as the hydrosilane at 100 °C.
doi_str_mv 10.1021/acs.organomet.5b00553
format Article
fullrecord <record><control><sourceid>hal_cross</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_01205446v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>oai_HAL_hal_01205446v1</sourcerecordid><originalsourceid>FETCH-LOGICAL-c353t-b804a74bb3d07d309a162ad5e3b2c374502ca22b10d3a81b890e0dc93eec3a2f3</originalsourceid><addsrcrecordid>eNo9kUtOwzAQhi0EEuVxBCRvkUgZ23HSsivhUUQFSMA6mthTakjjyo4Q4RLchgtwMQJFrEaa-b-ZkT7GDgQMBUhxjCYOfXjCxi-pHeoKQGu1wQZCS0gySMUmG4DMsyRXSm2znRifASDLlRywj-vm67N-oZA8dCviV8E3vPDLVU1vFPkpYXDNE8eG3yRTail405naGV5gqKghPnP9XXvC77umXVB08YgXCwxo-qx7x9b55qjHbQ-0WHdtj57RorPhd8T9nN8Ft8TQ8cnSWYp7bGuOdaT9v7rLHi_OH4ppMru9vComs8QordqkGkGKeVpVykJuFYxRZBKtJlVJo_JUgzQoZSXAKhyJajQGAmvGisgolHO1yw7XexdYl6v1C6VHV04ns_KnB0KCTtPsVfRZvc6a4GMMNP8HBJQ_BsreQPlvoPwzoL4BSxmAYw</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Knölker-Type Iron Complexes Bearing an N-Heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides</title><source>ACS Publications</source><creator>Elangovan, Saravanakumar ; Quintero-Duque, Samuel ; Dorcet, Vincent ; Roisnel, Thierry ; Norel, Lucie ; Darcel, Christophe ; Sortais, Jean-Baptiste</creator><creatorcontrib>Elangovan, Saravanakumar ; Quintero-Duque, Samuel ; Dorcet, Vincent ; Roisnel, Thierry ; Norel, Lucie ; Darcel, Christophe ; Sortais, Jean-Baptiste</creatorcontrib><description>A family of iron Knolker-type complexes bearing an N-heterocyclic carbene (NHC) ligand has been synthesized from the corresponding tricarbonyl(η4-cyclopentadienone)iron complex by reaction with the in situ generated NHC ligand, under UV irradn. (350 nm) at room temp. The six complexes, obtained in good yields (64-84%) after purifn. on column chromatog., were fully characterized, including X-ray diffraction and electrochem. studies. The activity of these complexes in catalysis has been demonstrated for the dehydration of primary benzamides into benzonitriles under hydrosilylation conditions using inexpensive polymethylhydrosiloxane (PMHS) as the hydrosilane at 100 °C.</description><identifier>ISSN: 0276-7333</identifier><identifier>EISSN: 1520-6041</identifier><identifier>DOI: 10.1021/acs.organomet.5b00553</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>Chemical Sciences</subject><ispartof>Organometallics, 2015-09, Vol.34 (18), p.4521-4528</ispartof><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-b804a74bb3d07d309a162ad5e3b2c374502ca22b10d3a81b890e0dc93eec3a2f3</citedby><cites>FETCH-LOGICAL-c353t-b804a74bb3d07d309a162ad5e3b2c374502ca22b10d3a81b890e0dc93eec3a2f3</cites><orcidid>0000-0003-1178-8588 ; 0000-0002-6088-4472 ; 0000-0001-6711-5978 ; 0000-0001-6654-1211</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,2765,27924,27925</link.rule.ids><backlink>$$Uhttps://univ-rennes.hal.science/hal-01205446$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Elangovan, Saravanakumar</creatorcontrib><creatorcontrib>Quintero-Duque, Samuel</creatorcontrib><creatorcontrib>Dorcet, Vincent</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Norel, Lucie</creatorcontrib><creatorcontrib>Darcel, Christophe</creatorcontrib><creatorcontrib>Sortais, Jean-Baptiste</creatorcontrib><title>Knölker-Type Iron Complexes Bearing an N-Heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides</title><title>Organometallics</title><description>A family of iron Knolker-type complexes bearing an N-heterocyclic carbene (NHC) ligand has been synthesized from the corresponding tricarbonyl(η4-cyclopentadienone)iron complex by reaction with the in situ generated NHC ligand, under UV irradn. (350 nm) at room temp. The six complexes, obtained in good yields (64-84%) after purifn. on column chromatog., were fully characterized, including X-ray diffraction and electrochem. studies. The activity of these complexes in catalysis has been demonstrated for the dehydration of primary benzamides into benzonitriles under hydrosilylation conditions using inexpensive polymethylhydrosiloxane (PMHS) as the hydrosilane at 100 °C.</description><subject>Chemical Sciences</subject><issn>0276-7333</issn><issn>1520-6041</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNo9kUtOwzAQhi0EEuVxBCRvkUgZ23HSsivhUUQFSMA6mthTakjjyo4Q4RLchgtwMQJFrEaa-b-ZkT7GDgQMBUhxjCYOfXjCxi-pHeoKQGu1wQZCS0gySMUmG4DMsyRXSm2znRifASDLlRywj-vm67N-oZA8dCviV8E3vPDLVU1vFPkpYXDNE8eG3yRTail405naGV5gqKghPnP9XXvC77umXVB08YgXCwxo-qx7x9b55qjHbQ-0WHdtj57RorPhd8T9nN8Ft8TQ8cnSWYp7bGuOdaT9v7rLHi_OH4ppMru9vComs8QordqkGkGKeVpVykJuFYxRZBKtJlVJo_JUgzQoZSXAKhyJajQGAmvGisgolHO1yw7XexdYl6v1C6VHV04ns_KnB0KCTtPsVfRZvc6a4GMMNP8HBJQ_BsreQPlvoPwzoL4BSxmAYw</recordid><startdate>20150928</startdate><enddate>20150928</enddate><creator>Elangovan, Saravanakumar</creator><creator>Quintero-Duque, Samuel</creator><creator>Dorcet, Vincent</creator><creator>Roisnel, Thierry</creator><creator>Norel, Lucie</creator><creator>Darcel, Christophe</creator><creator>Sortais, Jean-Baptiste</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-1178-8588</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0001-6711-5978</orcidid><orcidid>https://orcid.org/0000-0001-6654-1211</orcidid></search><sort><creationdate>20150928</creationdate><title>Knölker-Type Iron Complexes Bearing an N-Heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides</title><author>Elangovan, Saravanakumar ; Quintero-Duque, Samuel ; Dorcet, Vincent ; Roisnel, Thierry ; Norel, Lucie ; Darcel, Christophe ; Sortais, Jean-Baptiste</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-b804a74bb3d07d309a162ad5e3b2c374502ca22b10d3a81b890e0dc93eec3a2f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Chemical Sciences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Elangovan, Saravanakumar</creatorcontrib><creatorcontrib>Quintero-Duque, Samuel</creatorcontrib><creatorcontrib>Dorcet, Vincent</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Norel, Lucie</creatorcontrib><creatorcontrib>Darcel, Christophe</creatorcontrib><creatorcontrib>Sortais, Jean-Baptiste</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Organometallics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Elangovan, Saravanakumar</au><au>Quintero-Duque, Samuel</au><au>Dorcet, Vincent</au><au>Roisnel, Thierry</au><au>Norel, Lucie</au><au>Darcel, Christophe</au><au>Sortais, Jean-Baptiste</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Knölker-Type Iron Complexes Bearing an N-Heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides</atitle><jtitle>Organometallics</jtitle><date>2015-09-28</date><risdate>2015</risdate><volume>34</volume><issue>18</issue><spage>4521</spage><epage>4528</epage><pages>4521-4528</pages><issn>0276-7333</issn><eissn>1520-6041</eissn><abstract>A family of iron Knolker-type complexes bearing an N-heterocyclic carbene (NHC) ligand has been synthesized from the corresponding tricarbonyl(η4-cyclopentadienone)iron complex by reaction with the in situ generated NHC ligand, under UV irradn. (350 nm) at room temp. The six complexes, obtained in good yields (64-84%) after purifn. on column chromatog., were fully characterized, including X-ray diffraction and electrochem. studies. The activity of these complexes in catalysis has been demonstrated for the dehydration of primary benzamides into benzonitriles under hydrosilylation conditions using inexpensive polymethylhydrosiloxane (PMHS) as the hydrosilane at 100 °C.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.organomet.5b00553</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-1178-8588</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0001-6711-5978</orcidid><orcidid>https://orcid.org/0000-0001-6654-1211</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0276-7333
ispartof Organometallics, 2015-09, Vol.34 (18), p.4521-4528
issn 0276-7333
1520-6041
language eng
recordid cdi_hal_primary_oai_HAL_hal_01205446v1
source ACS Publications
subjects Chemical Sciences
title Knölker-Type Iron Complexes Bearing an N-Heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T04%3A45%3A35IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-hal_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Kn%C3%B6lker-Type%20Iron%20Complexes%20Bearing%20an%20N-Heterocyclic%20Carbene%20Ligand:%20Synthesis,%20Characterization,%20and%20Catalytic%20Dehydration%20of%20Primary%20Amides&rft.jtitle=Organometallics&rft.au=Elangovan,%20Saravanakumar&rft.date=2015-09-28&rft.volume=34&rft.issue=18&rft.spage=4521&rft.epage=4528&rft.pages=4521-4528&rft.issn=0276-7333&rft.eissn=1520-6041&rft_id=info:doi/10.1021/acs.organomet.5b00553&rft_dat=%3Chal_cross%3Eoai_HAL_hal_01205446v1%3C/hal_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true